Pyridine → HCID 22598274, compound

HRID 1369348Notes

Reaction equation

[CH2:1]([N:5]([C:17]1[N:22]=[C:21]([N:23]([CH:28]2[CH2:33][C:32]([CH3:35])([CH3:34])[N:31]([OH:36])[C:30]([CH3:38])([CH3:37])[CH2:29]2)[CH2:24][CH2:25][CH2:26][CH3:27])[N:20]=[C:19]([Cl:39])[N:18]=1)[CH:6]1[CH2:11][C:10]([CH3:13])([CH3:12])[N:9]([OH:14])[C:8]([CH3:16])([CH3:15])[CH2:7]1)[CH2:2][CH2:3][CH3:4].N(O[C:43]([CH3:46])([CH3:45])C)=O.N[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1.N1C=C[CH:57]=[CH:56][CH:55]=1>>[CH2:1]([N:5]([C:17]1[N:22]=[C:21]([N:23]([CH:28]2[CH2:33][C:32]([CH3:35])([CH3:34])[N:31]([O:36][C:45]3[CH:43]=[CH:46][CH:57]=[CH:56][CH:55]=3)[C:30]([CH3:37])([CH3:38])[CH2:29]2)[CH2:24][CH2:25][CH2:26][CH3:27])[N:20]=[C:19]([Cl:39])[N:18]=1)[CH:6]1[CH2:11][C:10]([CH3:12])([CH3:13])[N:9]([O:14][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[C:8]([CH3:15])([CH3:16])[CH2:7]1)[CH2:2][CH2:3][CH3:4]

Participants

Reactant 4

HCID 1049Pyridine

HCID 6115Aniline

HCID 10906Tert-Butyl nitrite

HCID 58330421HCID 58330421, compound

Product 1

HCID 22598274HCID 22598274, compoundYield 60.5%

Procedure

The procedure of Example 1 is repeated using 3.89 g (6.90 mmol) of 2,4-bis[N-butyl-N-(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)amino]-6-chloro-s-triazine, 3.29 g (32 mmol) of tert-butyl nitrite, 4.2 mg (0.0069 mmol) of (S,S)-(+)-N,N-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(II), 120 mL of pyridine and 2.56 g (27.6 mmol) of aniline at 70° C. The crude product obtained is purified by vacuum flash chromatography (heptane) to give 3.0 g of the title compound as an off-white solid in 60.5% yield.

Workup

customat 70° C
customThe crude product obtained
customis purified by vacuum flash chromatography (heptane)

Sources & evidence

ORD record: ord-3375a7a17f624c26be116be8ac47396c
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06579328B2

Reaction notes

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